Facile Synthesis of Furowarfarins via Hetero-Diels-Alder Cycloaddition Reaction

Synthesis of new furowarfarins has been carried out via tandem Knoevenagel-hetero-Diels-Alder cycloaddition reaction. One-pot, multicomponent reaction involving, heating a mixture of hydroxy chromenone, aldehyde, and 2-methoxy propene afforded pyranochromenone with good diastereoselectivity, favorin...

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Bibliographic Details
Published in:Synthetic communications 2013-02, Vol.43 (6), p.775-783
Main Authors: Soman, Shubhangi S., Patel, Jagdish M.
Format: Article
Language:English
Subjects:
Exo (trans)
furowarfarin
half-chair conformation
Knoevenagel-hetero-Diels-Alder cycloaddition
x-ray crystallography
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Summary:Synthesis of new furowarfarins has been carried out via tandem Knoevenagel-hetero-Diels-Alder cycloaddition reaction. One-pot, multicomponent reaction involving, heating a mixture of hydroxy chromenone, aldehyde, and 2-methoxy propene afforded pyranochromenone with good diastereoselectivity, favoring the exo (trans) cycloadduct, in contrast to previous literature reports. The pyran ring exists in a half-chair conformation with C9-OMe in ψ -axial and C7-phenyl ring in ψ -equatorial positions. Single-crystal x-ray analysis conclusively confirms the structure.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2011.609302